A good pivot is like going home. It's warmer, it's closer to something that you're an expert at.
Pivot toward expertise, not away from pain
Strategy → Roadmaps & Planning
If it's not going well and you're out of ideas, that is usually a good time to pivot. But when you have half a dozen or a dozen really good growth ideas that you haven't tried yet, try them.
Going from one to two products is hard. Going from two to end is much easier, but going from one to two is hard.
Product market fit is just the product, and that is not a company, and that will not scale.
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